Modesty
by aachannoichi
Summary: Living and training together can be difficult at times. Today was one of those challenging moments when The Boss finds Jack in a rather compromising situation. But instead of getting angry, The Boss uses this awkward moment to break Jack of his modesty.


Modesty

Stretching, The Boss got up from her chair and walked out of the den. She had spent all day reading various files and catching up on lingering paperwork. God how she hated doing mindless paperwork, but it was one of those mundane things that had to be done. Even the legendary Boss wasn't immune to a mound of paperwork. However after working several hours without interruption it was time for a much needed break. She needed to get something to eat and drink, plus she figured it would best if she checked on Jack to see what he was up too.

Around seven in the morning she heard him finally wake up and shower. Hopefully he had done at least half of his chores this morning. Wood needed to be chopped for the fire. The car they shared needed to be washed. Then there was the leaky faucet in kitchen sink which she had demanded to be fixed for a few days now. Sometimes Jack was like a child who needed constant supervision and chiding. Just the thought of Jack loafing around today made her blood boil. If he was lazing around today, there would be hell to pay.

Walking around the hallways of their home The Boss began to question if Jack was even in the house; everything seemed really quite and still. But he couldn't be gone; she didn't hear the front or back doors close, nor did she hear the car start up and take off. Besides he knew better then to take the car without her permission. Also she could feel a second presence in the house, but she wasn't sure where exactly he was hiding.

"Jack?" She questioned as she passed by their bedroom. "Jack, are you in here?"

Opening up the door their bedroom she didn't see him in here. Well, at least he wasn't in here sleeping. Closing the door, she walked down the hallway and passed by the bathroom. As she walked by, she could hear a strange sound. It was the sound of breathing- heavy breathing. At first The Boss was perplexed by the sound of shallow breathing. They hadn't been training today, and he couldn't have done anything strenuous to cause him to breathe so heavily. Finally it occurred to her what exactly what Jack may be doing.

" _Oh he couldn't be…_ " She thought for a moment.

She stood by the door for a moment to make sure her suspicions weren't valid, but the breathing continued. Grabbing the door knob, The Boss opened the door and there on the toilet sat Jack, shirtless, with his pants and undergarments around his ankles, masturbating wildly to some photos.

"I thought that's what you were doing!" She said exploding through the door.

Instantly Jack stopped what he was doing and his face turned a deep shade of crimson.

"And you're doing it to pictures!" She said sounding disappointed. "Jack, no one likes a cheater."

"Boss…" He said with his deep voice cracking as he desperately attempted to cover up his genitals.

The Boss walked over to Jack and snatched the pictures from his free hand, then she thumbed through them. The first set of pictures were of a voluptuous young woman being penetrated by a rather well-endowed man. The second set was of the same woman orally gratifying that man. The final set of photos was of the man ejaculating on the young woman's very ample breast.

"I take it these came in the package Doug sent to you?" She questioned.

Jack was still highly embarrassed so he didn't answer her.

"I'll deal with Doug later." She said sternly. "As for you, you are going to learn a few things…"

"But, but…" Jack stuttered.

"I'll be keeping these photos." She said stuffing the photos into her pants pockets. "But in the meantime, I want you to finish what you were doing."

"Finish?" He said sounding completely mortified and his once crimson face suddenly turned pale.

"Yes." She said austerely. "Finish. Right now."

"But I…" Jack stammered again.

"But what?" She questioned.

"I can't…" He answered nearly imperceptibly.

"Why can't you." The Boss questioned.

"I…" He choked on his words. "I just can't."

"Is it because you don't have your pretty pictures?" She questioned. "Or is there another reason?"

He didn't answer her.

"Just look at how embarrassed you are right now." She said sternly. "A solider has no shame, no modesty. You should be able to do anything, no matter what it is without being nervous."

Jack had nothing to say.

"You are going to stand up right now and finish masturbating in front of me!" The Boss demanded.

"Boss?!" Jack was appalled by such a brazen request.

"Go on." She commanded. "I want you to finish right now."

Jack stood up and then looked down at his manhood, but he knew as long as she was standing there staring through him he, would never be able to get aroused. Besides, it was really difficult for him to just instantly get aroused. He needed some form of outside stimulus or at a low an idea worth getting sexually aroused by. Looking back up at The Boss he saw "the look". "The look" was something he was all too well acquainted with and something that filled his blood with icicles. When The Boss was displeased, she was capable of anything. There was a very real fear that if he didn't produce some kind of results, she may just yank his genitals off. The thought of her yanking off his manhood sent glacial chills throughout Jack's entire body, further dampening his hopes of becoming even the slightest aroused.

"I'm waiting." She said impatiently.

Jack looked down at his manhood again but nothing was happening. It was as if his blood had been frozen in place and refused to return to his flaccid manhood. Deep down his was always afraid of The Boss, but this went beyond his usual nervous tension. This was absolute hysterical fear and it was completely evident. The Boss was aware of what Jack was feeling and she just shook her head in disappointment.

"Pull up your pants and come with me." She charged.

Jack gulped and reluctantly pulled up his pants and undergarments. The Boss led Jack out of the bathroom towards their bedroom. She opened up the bedroom door and went instantly over to the bed. Sitting down upon the mattress, she beckoned Jack to come inside. Sheepishly, Jack walked into the room and stood in front of her hanging his head in shame.

"Now then." She said sternly. "I want you to understand something, if you want to be a solider you are going to have drop the modesty routine. There could be a time when you are captured by an enemy, stripped naked, and forced to partake in some… Let's just say very unpleasant acts. You won't have time for modesty then will you?"

"No Boss." Jack replied practically inaudibly.

"What was that?" She questioned unsympathetically.

"No Boss!" He said in a more solider-like tone.

"With that being said, I want you to take off all your clothes right now."

Jack began to undress. First Jack unlaced his shoes and place them neatly in a nearby corner. He then unbuckled his black leather belt, and unbuttoned his trousers to let them fall to his ankles. Stepping out of them he picked them up folded them neatly and draped them over a nearby chair. When he was finished with that task he waited for instruction from The Boss.

"I said takeoff ALL your clothes Jack." She said sternly as she eyed his stark white underpants.

Once again, Jack's face turned a bright shade of red as he pulled down his white underpants and let them slide to his ankles before stepping out of them. His entire body scorched with discomfiture, naturally he tried to cover up his genitals from The Boss's view.

"Put your hands at your side Jack." The Boss demanded.

With a sigh and a gulp, Jack put his arms at his side. The Boss couldn't help but smile at the view she was treated to. Astonishingly, Jack was pretty well endowed. Someone with as insolent and at times obnoxious as he was didn't seem like the type with the manhood to back it up. It was indeed very impressive, and this was even before he was aroused. Imagine what it would look like when he was at his full height?

The Boss got up from the bed and walked over to Jack, who was obviously mortified beyond anything he had ever known. But someday he would learn to shake off that modesty, however this first hurdle needed to be crossed.

"How old were you when you lost your virginity Jack?" She asked walking around him, eyeing up his body like a hungry lioness circling her prey.

"I was 17." He said softly.

"That's about the average age." She said gently. "Who was she?"

"Catherine Berkley." Jack answered retrieving some of the vibrato in his voice.

"Pretty name." The Boss answered. "Was she pretty?"

"Yes." He answered with is voice changing to a more nostalgic tone.

"What did she look like?" The Boss asked as she stopped behind him and slowly slid her hands across his broad back.

"She…" He stuttered a moment. The Boss's hands felt so good against his back. They were so warm and surprisingly soft. It was strange to actually have her be gentle with him, but it also felt so very good. "She had long brown hair, big brown eyes, this bright sunny smile…"

"Did she have a nice body?" The Boss questioned continuing to rub his back.

"Yes." He said sighing softly.

"Tell me about it." She commanded, but in a soft tone.

"She had very plump breast. A thin waist and nicely shaped backside."

"Tell me about your first time?" The Boss whispered. "How did it happen?"

"It was the day of my high school senior class picnic." He started. "It was being held at this lake in my hometown. I remember it was a warm sunny day, and Catherine had on this pink and white dress, she looked so pretty when I picked her up that day…"

Jack paused for a moment. He could feel The Boss moving her hands from his back to his muscular chest, and then slid down to his semi-aroused member. The chills from her masturbating him were maddening.

"Keep going Jack." She whispered in his ear.

"We get half way to where the picnic was when Cathy tells me to pull over. I asked her why and she showed me that she wasn't wearing any panties."

"Interesting." The Boss said raising an eyebrow to his last statement. "She was a very bold young lady. Please continue."

"So I pulled over and she lets me look up her skirt." Jack continued with his story. "Shortly after that we started making out pretty heavy. So finally she takes off her dress and bra, I undress and we both climb in the back seat of my car."

The Boss took one of Jack's hands and placed it to his manhood, but she didn't remove her hand, she wanted to help him masturbate, at least for a little while.

"How did your first time feel Jack?" The Boss asked.

"So very good." He said breathlessly. "I remember when I first entered her… It was so warm and moist inside of her. I thought I was going to go insane."

The Boss let go of his hand, but Jack didn't even notice. He was so into the story that it didn't even occur to him that The Boss was no longer guiding his hand.

"So I take it she was quite good then?" The Boss said as she watched him masturbate from behind.

"She was." He said beginning to pant wildly. "Her plump breasts bounced as I drove into her… And her eyes… When they looked up at me… They were the most beautiful blue you had ever seen."

"Really?" The Boss questioned suspiciously.

"Yes." He answered softly. "Just like the color of the tropical sea."

The Boss knew that he was no longer thinking of his former girlfriend, but his mind was now drifting to thoughts of her. But before she could pull any more information out of him, his body began to convulse and she knew he was reaching orgasm. Finally, Jack closed his blue eyes and groaned as his lust exploded from his body. The Boss smiled, finally this was one hurdle he crossed, but there was still a lot of work to be done on him.

"Come Jack." She said sweetly. "Lie down with me."

Jack was spent, he barely had the energy to make the four step walk over to the bed, but he somehow managed to do it without toppling to the floor. The Boss lay down on the soft mattress and Jack lay on top of her. He hated to admit it, but it felt good to be nestled up against her breast. Plus she smelled like honeysuckle, it was one of his favorite smells. Secretly it was one of the things that really made Jack like her.

The Boss took one arm and wrapped it across Jack's back and with her other arm, she gently stroked and caressed his dark brown hair. She could feel his arms start to drop to her sides. He wanted to hold her, but he was reluctant, she didn't want to force his affections, so she just continued to stroke his hair. After a short while, Jack began to relax and he gently held The Boss, which instantly brought a smile to her face.


End file.
